The Synthesis of Bromomethyltrifluoroborates through Continuous Flow Chemistry

Broom, Toby; Hughes, Mark; Szczepankiewicz, Bruce G.; Ace, Karl; Hagger, Ben; Lacking, Gary; Chima, Ranjit; Marchbank, Graeme; Alford, Gareth; Evans, Paul; Cunningham, Christopher; Roberts, John C.; Perni, Robert B.; Berry, Malcolm; Rutter, Andrew; Watson, Simon A

The Synthesis of Bromomethyltrifluoroborates through Continuous Flow Chemistry

By Broom, Toby; Hughes, Mark; Szczepankiewicz, Bruce G.; Ace, Karl; Hagger, Ben; Lacking, Gary; Chima, Ranjit; Marchbank, Graeme; Alford, Gareth; Evans, Paul; Cunningham, Christopher; Roberts, John C.; Perni, Robert B.; Berry, Malcolm; Rutter, Andrew; Watson, Simon A

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Published on CMKC

23 Jul 2024

Abstract

A continuous flow process was developed for the synthesis of potassium bromomethyltrifluoroborate, a key precursor for Suzuki–Miyaura coupling reagents. The continuous flow process was used to produce potassium bromomethyltrifluoroborate on scales from grams to kilograms, and the successful process utilized a fraction of the resources required for the batch synthesis. In the plant, a team of three people produced approximately 100 kg of potassium bromomethyltrifluoroborate in less than 4 weeks. This process makes it both practical and economical to use potassium bromomethyltrifluoroborate and its derivatives for multikilogram-scale Suzuki–Miyaura couplings.

Journal

Organic Process Research & Development. Volume 18, 2014, 1354–1359

DOI

10.1021/op400090a

Type of publication

Peer-reviewed journal

Affiliations

GlaxoSmithKline
Sirtris
Glaxo Operations UK

Article Classification

Research Article

Classification Areas

Intermediate